Hydrochloric Acid → HCID 11307987, compound

HRID 915283Notes

Reaction equation

HRID 915283 reaction equation
[C:1]([N:4]([CH2:25][C@@H:26]1[O:30][C:29](=[O:31])[N:28]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]3[CH2:43][CH2:42][S:41](=[O:45])(=[O:44])[CH2:40][CH2:39]3)=[C:34]([F:46])[CH:33]=2)[CH2:27]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:24])[C@@H:11]([NH:16]C(OC(C)(C)C)=O)[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.C1COCC1.[ClH:60]>CCOCC>[ClH:60].[C:1]([N:4]([CH2:25][C@@H:26]1[O:30][C:29](=[O:31])[N:28]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]3[CH2:39][CH2:40][S:41](=[O:44])(=[O:45])[CH2:42][CH2:43]3)=[C:34]([F:46])[CH:33]=2)[CH2:27]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:24])[C@@H:11]([NH2:16])[CH2:12][CH:13]([CH3:14])[CH3:15])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8028TetrahydrofuranHCID 11319865HCID 11319865, compound

Product 1

HCID 11307987HCID 11307987, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2(S)-tert-Butoxycarbonylamino-4-methyl-pentanoic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12e) (0.35 g, 0.52 mmol), anisole (0.5 mL) and THF (10 mL), is added hydrogen chloride (4 M in dioxane, 4 mL, 15.7 mmol) in a dropwise manner. The mixture is stirred at RT overnight. Ether is then added dropwise to the mixture while stirring. Under reduced pressure, the mixture is concentrated to one-third of its original volume. Ether is again added, resulting in the formation of a solid. The solid is collected via filtration, rinsed with ether and ethyl acetate, and dried under vacuum to give the title compound in 39% yield (0.12 g). 1H NMR (400 MHz, CD3OD): δ 7.52 (dd, 1H), 7.37 (t, 1H), 7.26 (dd, 1H), 6.02 (ABq, 2H), 4.88 (m, 1H), 4.20 (m, 3H), 4.10 (dd, 1H), 3.83 (m, 1H), 3.35 (m, 2H), 3.23 (tt, 1H), 3.12 (m, 2H), 2.54 (s, 3H), 2.35 (m, 2H), 2.17 (m, 2H), 1.85 (m, 2H), 1.72 (m, 1H), 1.02 (d, 3H), 1.01 (d, 3H). MS-APCI (m/z+): 341, 385, 572.

Workup

  1. stirringwhile stirring
  2. concentrationUnder reduced pressure, the mixture is concentrated to one-third of its original volume
  3. additionEther is again added
  4. customresulting in the formation of a solid
  5. filtrationThe solid is collected via filtration
  6. washrinsed with ether and ethyl acetate
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b8b0909e3cf749f18c08d336e28065f6
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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